A week ago, my friend Jack Raines published a book called Young Money. He has this knack for telling great stories that both make you laugh and make you think. Not many people can do what he does, so I asked him to tear apart the story he tells in chapter 1 to show you exactly why it works and how the storyteller thought about building it. Enjoy.
In the real-world, I have a selection of tried-and-true “stories” that I know play well in different settings. Happy hour stories guaranteed to draw a few laughs. Date stories that pierce the “hedged” conversation topics of early engagements and either A) kick off a round of increasingly irreverent banter or B) lead to a nervous laugh and “I might need to head home soon.” “New friend” stories that cause my existing friends to groan after they’ve heard them 15 times, but the new entrant finds wildly entertaining. Podcast stories that I tell on shows.
I know which of these stories flop in which situation, and how to lengthen, shorten, and otherwise adjust these stories in-flight.
I also have “written” stories, many of which appear in my book, Young Money: A Field Guide to Wealth and Purpose in Your Twenties. Written stories are a bit different than spoken stories because you can edit them. You can change verb tenses, add and remove context to shape the reader experience.
There’s more pressure on a written story, particularly when told in a book, than a live story. If a live story flops, you can adjust accordingly in the next conversation. But a book is permanent, meaning that every story in the 60,000+ words must delight the reader and move the book forward. Live stories are perfected over the course of multiple conversations. Written stories are perfected over the course of multiple revisions.
I think it’s more helpful to both explain the reasoning behind a specific story within the context of a broader work, rather than discuss “storytelling” in the abstract.
So let’s take the opening passage from my book.
(The actual passage is in black. My comments on the “reason” behind the structure and other choices are in red. Nathan will leave a few observations in blue.)
Chapter 1: The Opportunity Cost of Everything
Every young person should blow up their life at least once.
Not in an “I developed a substance-abuse problem and had to go to rehab for a few months” way, but in an “I’m willing and able to uproot foundational aspects of my life and try something new” way.
I’ve blown up my life twice.
Every chapter opening needs to hook the reader, but this is especially true with the first chapter.
The engagement you deliver with chapter one buys you goodwill to be flexible with the rest of the book. But chapter 1 has to hook the reader. And the opening paragraphs of each subsequent chapter must re-engage the reader as well.
I open with a provocative statement. Maybe you agree with it. Maybe you disagree with it. But it’s an unhedged declaration that sets the tone for the rest of the book. I then, immediately, follow that up with light humor that simultaneously takes off the edge while beginning to establish my voice.
“I’ve blown up my life twice.” tells you that this declaration is rooted in my own experience, which this opener served to prepare the reader to receive.
//
Jack has made a promise. Both in terms of what tone you’re getting the rest of his story as well as what you’re going to hear about - the two times he blew up his life. Always ask: what promise am I making here? Especially at the start of your story.
The first time was in May 2021, when I was twenty-four. The second time was in January 2025, when I was twenty-seven. Most of what you will read over the next ~250 pages relates to my life experiences and reflections between those points, but for now, let’s focus on that first instance.
What happened in May 2021?
It was 8:18 p.m. on a Friday evening in Atlanta, Georgia. I was supposed to meet friends for dinner in twelve minutes at a tapas restaurant twenty 20 minutes away, and I was going to be lucky if I made it there by nine. The reason for my delay?
Work, obviously.
If you’ve ever worked in a job where your responsibilities, schedule, and expectations appeared to defy the laws of logic and sensibility, this story might hit close to home. I was a financial analyst for America’s largest logistics company, and for the third Friday in a row my eyes were glazing over as I worked well into the night to update a deck reflecting some trivial change in UPS’s hypothetical financial situation seven months out.
More specifically, I was halfway through the twelfth revision of an Excel model that showed how UPS’s Q4 2021 operating profit in North America could be $4 million lower if jet-fuel prices increased by $0.27. Or something like that. Who cares. The details, like the model itself, don’t matter all that much.
Which was the problem.
Context-setting.
To appreciate my story, you need to know the ‘version’ of me that’s telling the story. From the cuff, you know that this is a 24-year-old guy, who, from the prior section, is probably a bit sarcastic. By the end of this section, a lot of readers find something relatable: a 20-something dude cranking out nonsense on Excel sheets that he couldn’t care less about.
This paragraph both gives the reader an image of who “I” am, while also painting a clear picture of the life I was living, down to an incredibly specific example of modeling Q4 2021 operating profit.
//
You get the surface level conflict immediately. Worker stuck at work on a Friday night. You also know Jack’s about to blow up his life somehow. That creates a gap, and you wanna see how he goes from one to the other.
This is ridiculous, I thought. I glanced at the time on my phone: 8:18 p.m.
My coworker, Michael, was trying his best to remain upbeat on the other side of the Zoom call, but we were caught in a prisoner’s dilemma where we both knew that our current predicament was neither necessary nor important. Yet neither of us was willing to voice those opinions aloud. So, instead, we sat at our respective desks, going on hour eight of expressing the feigned cheerfulness that plagued pandemic-era remote work.
I had, at this point, updated cell E11 no fewer than fourteen times, and I glanced at the ceiling fan in the reflection of my Zoom camera, wondering if it could support my 225-pound frame. That would have added some excitement to Michael’s evening, anyway.
Why was I, for the third Friday in a row, going on hour 8 of updating this spreadsheet? Because UPS’s finance department required all teams to submit their weekly reports every Friday. This mandate ignored two small, but for my team, critical details:
(1) Eighty percent of the inputs my team needed for our models came from other groups that didn’t submit their reports until Friday, which meant that we couldn’t make any meaningful progress on our reports until, well, Friday.
(2) There weren’t any pressing reasons that implored us to turn our work around on Friday. We were modeling airline-fuel prices seven months in the future, not stopping terrorist attacks. Time was absolutely not of the essence.
Not that any of that mattered to my director. So after spending Monday through Thursday sending around trivial emails, scrolling Reddit, and moving my mouse every six minutes and forty-five seconds to remain “active” on Slack, I would speed-run an entire week’s worth of work between ~12 p.m. and 8:30 p.m. every Friday.
Four years later, I still get frustrated thinking back on the inefficiency of it all, but that is, unfortunately, how corporate bureaucracies work.
This scene is like a scene from the British version of The Office. Dark sarcasm applied to mundane existence. I want the scene to be both hyper-realistic (a couple of employees who both hate being stuck on Zoom but have to fake being upbeat), triple down on the over-specificity of examining Excel cells and faking activity on Slack to prove the point, then make an abstract allusion to death-by-ceiling fan to draw a chuckle out of the reader.
The goal here was to amplify the mundaneness of my existence while making it as relatable as possible to the reader. Who amongst us hasn’t found themselves silently suffering in white collar mundanity? Who hasn’t dealt with bureaucratic policy hell?
I did eventually make it to dinner, and after delivering apologies for my tardiness, I settled in for a fun night with friends. However, as I got ready for bed that night, my frustrations from earlier that evening gave way to late-night introspection.
Although I was irritated that my plans for the last three Friday evenings had been disrupted, it wasn’t the inconsiderate timing of my deadlines that really bugged me. The real issue, which had been gnawing at me for weeks, was that these tasks didn’t really matter. And more importantly, they were crowding out things that did.
Transition. We have a brief resolution to our late-work-on-Friday conflict, then the goal is to move from describing my current environment and real-time frustration to inspecting my psyche: the “small” issue of inconvenient scheduling is a symptom of a much larger problem of existential malaise, which will begin to set the theme of the book: how do I make the most of my time in this current stage of life?
To recap: hook the reader with an aggressive statement, establish my irreverent tone as quickly as possible, suck the reader into my world of corporate hell, then start peeling back the layers of what, exactly, is going on in Jack’s mind?
//
Deeper conflict. Surface level conflict - missing dinner for work - isn’t all that interesting. Here Jack starts to ask why he’s really bothered.
For any conflict in your stories, ask why you or the character care. That’s probably the real heart of the story, not whatever’s on the surface.
The lie that you’re told as a twenty-two-year-old on the cusp of graduating from college is that your career will be this exciting journey where you might make a difference in the world. But the reality of my situation as a twenty-four-year-old financial analyst eighteen months into his career was that I was spending my Friday evenings copying numbers from fifteen different emails to paste them in Excel spreadsheets to generate new numbers that I would then copy and paste in another email to someone else.
I’m sure that the poor soul on the receiving end of that email couldn’t have cared any more about my fuel-price projection than I did, yet his job was probably to copy and paste my numbers into some other spreadsheet to generate some other numbers before sending his numbers to someone else, and the cycle would just keep going and going until I would send a new number the next week.
It was so fucking stupid. And for what, $60,000 a year?
Frustration. Frustration. Frustration. And this is the frustration that should resonate with readers who are in, or who have been in, similar situations. Mock the situation: play out the hypothetical, imagining another version of myself playing “Excel hot potato” with my file.
“It was so fucking stupid.” Cursing is powerful when used with restraint. Once every 10,000 words will suffice. Any more, and the word loses it’s edge. Use it to catch the reader’s eyes. Provide a bit of shock value. Then drop it for a few chapters.
Still, I don’t mean to sound pretentious. I was a twenty-four-year-old guy with an email job I could do in my sweatpants, and spending a few Fridays working late thanks to my boss’s inconvenient scheduling preferences shouldn’t have been the end of the world.
Lying in bed that night, however, I realized that my Friday-evening fire drills weren’t outliers in their irrelevance. They simply highlighted a truth that I had spent the last eighteen months attempting to suppress: The last year and a half of my life had been a complete waste of time.
Thanks to COVID-19, every single day since starting my job in February 2020 had looked the same: I would roll out of bed, throw on some sweatpants, make a pot of coffee, respond to a few emails, manipulate Excel sheets and PowerPoints, send those models and decks around to my team, further revise those models and decks, feign interest in Zoom calls, and move my mouse to appear “online” regardless of how much work actually needed to be done.
I wasn’t being compensated for my skills; I was being compensated for my obedience. And as I stared at my ceiling, one thought wouldn’t stop ringing through my mind:
You’re wasting your time.
And once that thought materialized, it metastasized like a cancer. My mind was racing:
You’re not just wasting your time. You’re wasting your life. Is this just how it is? Move numbers around on reports at the mercy of someone else’s schedule for the next forty years? What’s the best-case scenario here? Maybe after twenty years, you get to be the guy in charge of everyone else’s reports instead? Just trading hours and days and weeks and months and years of white-collar bullshit for a check? That’s how we’re spending the next forty years? How stupid is that?
Can you see it? Can you see me trying to talk myself off the cliff? “You should be grateful for what you have,” I should be thinking. “My life is good. My struggles are first-world-problems. Just ignore the problems. They’re not real problems.”
But you can see it: you can picture me going through day after day of the same drudgery with a calendar flying by. January turns into February turns into March turns into April. Sweatpants. Coffee. Zoom calls. Repeat.
Now you can see me laying in bed. I’m trying to sleep. Can’t. There’s this existential dread building up inside me. Time is flying by. I’m not capturing it. What do I have to show for that passage of time? I’m a passive participant in my own life. When does it end? When does life begin? How did I get stuck?
This section is revealing my own anxiety in an attempt to relate to the reader’s anxiety. A lot of people have felt this, or are feeling this too. If you relate to it, you’ll keep reading, because you’re hoping that, at some point, we reach a resolution, because you’re looking for one of your own.
//
Now Jack’s asking why over and over. We’ve gone from the conflict being:
Missed dinner with friends to
His work doesn’t matter to
He’s wasting his time to
He’s wasting his life
I guarantee you these deeper layers of frustration resonate with his Reader far more. Look for yours in your stories.
So before I go any further, I want you to know that if you’ve ever asked yourself these same questions, you’re not crazy.
If you’ve found yourself fighting back tears after a miserable workweek where you struggled through projects that you couldn’t care less about, you’re not crazy. If you’re sick of living at the mercy of Slack pings and Teams notifications, you’re not crazy. If you dread checking your inbox on Monday morning, you’re not crazy. If you’ve ever taken a good, hard look at how you’re spending your days and asked yourself, What’s the point of it all?, you’re not crazy.
You’re just beginning to notice the opportunity cost of your time.
Now I call out to the reader directly. Break the fourth wall. At first I was telling my story. Then, before the reader realizes it, they realize that my story is, in fact, their story. Now I call out to that reader directly. Acknowledge the thing we’re both feeling. “I was dreading this thing. You might be too. You were trying to suppress it. Don’t do that. I felt it. You felt it. Other people feel it. We’ll get to the reason why it feels so existential, but you have to stick around.
Keep the reader engaged. Now they know that I “get” them, because I described their life through my life. The story can advance, the seed has been planted. The reader will want to know what comes next for the protagonist and author.
//
Jack introduces a concept “the opportunity cost of time” that his entire book centers upon, but doesn’t go any further. He just promises you’ll get more later. A very direct open loop.
In the weeks following my Friday-evening crash-out, I tried to ignore those thoughts. You just need to stick it out at UPS for another year, I told myself. And sticking it out, really, would have been the logical decision. It was May 2021, and I had already been accepted to business school at Columbia University in New York with plans to matriculate in August 2022. The “correct” path forward would have been to suck it up, stick around for another year, cop a promotion and a pay bump along the way, stack some cash, quit the following spring, and enjoy some time off before beginning graduate school.
But another twelve months of passive existence would have been a long time to “stick it out,” and with each additional day of Zoom calls, Excel revisions, and pointless meetings, that voice in my head grew louder.
You’re wasting your life, Jack! Is this really how you want to be spending your days, Jack?
But what was I supposed to do? Just quit? And then what? Around the time that my internal turmoil reached its fever pitch, I ran into my boss at a bar.
More context. Where is the narrator in his life? More context on why he “should” just suck it up and deal with the cards he’s been dealt. Rationalize. Rationalize. Rationalize.
But you know he’s going to do something to break the cycle. You can feel it building. His subconscious is screaming for him to do so. But what’s going to be the catalyst? We set the stage, and prepare to change scenes, where you know he’s going to have a conversation with his boss that permanently alters his current state.
Okay, class. Let’s review. This story was the opening ~3-4 pages of Young Money. This story served a few purposes:
Catch the reader’s attention. IMMEDIATELY. Without a strong opening sentence, and a passage that quickly builds off that sentence, you lose the reader. The first few paragraphs create momentum.
Establish my voice. Irreverent. Ironic. Dark humor, at times. You know you’ll see more of that. We describe the scene from the perspective of the author. What is seeing in the world around him? What stories is he telling himself? By paragraph five, the reader has a feel for both the author’s tone and his point-of-view when writing.
Resonate with readers who have had similar experiences. This book isn’t for everyone. That’s fine. But you want to tell a story with such precise details that the specifics of Excel sheets, fake Slack activity, and prisoner’s dilemma Zoom calls have some readers nodding their heads in agreement. Whether they’re living that existence now, or it took them back a few years, they’re now invested in my story because it, in some ways, reflects their own.
Context and vulnerability. A good story, particularly when told about the author’s own life, gives the reader a peak into “who” the author is, enabling them to better understand the book not just on the merit of its words but as the perspective of the person who write it. Don’t hedge when talking about your own life. Show your vulnerabilities so the reader will take you seriously. “I don’t have it figured out. This is my story. This isn’t self-help slop, it’s a human experience.” The story has stakes.
Transition to the “broader theme.” A lot of “non-fiction / self-help” follows the same cookie cutter pattern of “random historical anecdote is force-fit against lesson the writer wants to convey.” I think that structure is stupid. And it’s also why “self-help” is getting destroyed by AI: LLMs can do that just fine on their own. But if you tell a personal story to show how one’s own experience led to their revelation, the “idea” that you want the reader to understand feels natural, like talking to your friend at the bar. And that’s precisely how a “good” story should feel: like a conversation at a bar, two drinks deep, with a friend.
I don’t have any particular “rules” when it comes to telling stories, other than this: Any good story must entertain the reader. That entertainment might mean they laugh, it might mean their heart starts beating out of their chest. It might mean they nod in agreement, or they find themselves muttering, “what the hell is this guy talking about?” but they won’t be “bored.” If the reader is bored, you’re cooked. The reader needs to react. And that reaction is what compels them to turn another page.
And a great story? It provides a lesson that was never explicitly stated. The reader “figures out” the point on their own by virtue of reading about the author’s experience. That’s what stories are: a connection via shared human experiences.
Anyway, thanks for reading. And check out my book: Young Money: A Field Guide to Wealth and Purpose in Your Twenties.
Jack
Multi-colored text is aesthetically pleasing.
this is very cool - well done guys